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Literature DB >> 34062058

Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters.

Jianyu Xu¹, Olivia P Bercher¹, Mary P Watson¹.

Abstract

The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the "naphthyl requirement" that pervades stereospecific cross-couplings involving enantioenriched electrophiles.

Entities: Chemical

Mesh：

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Year: 2021 PMID： 34062058 PMCID： PMC8255275 DOI： 10.1021/jacs.1c03898

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 16.383

45 in total

1. Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling.

Authors: Chung-Yang Dennis Huang; Abigail G Doyle
Journal: J Am Chem Soc Date: 2015-04-24 Impact factor: 15.419

2. C-P bond-forming reactions via C-O/P-H cross-coupling catalyzed by nickel.

Authors: Jia Yang; Tieqiao Chen; Li-Biao Han
Journal: J Am Chem Soc Date: 2015-01-30 Impact factor: 15.419

3. Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions-alternatives to PtBu3.

Authors: Christoph A Fleckenstein; Herbert Plenio
Journal: Chem Soc Rev Date: 2009-10-16 Impact factor: 54.564

4. Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

Authors: Michael R Harris; Luke E Hanna; Margaret A Greene; Curtis E Moore; Elizabeth R Jarvo
Journal: J Am Chem Soc Date: 2013-02-22 Impact factor: 15.419

5. Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors: Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal: J Am Chem Soc Date: 2013-02-20 Impact factor: 15.419

Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters.

1. Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling.

2. C-P bond-forming reactions via C-O/P-H cross-coupling catalyzed by nickel.

3. Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions-alternatives to PtBu3.

4. Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

5. Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

6. Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands.

7. Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions.

8. Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.

9. Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

10. Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones.

1. Controlling Ni redox states by dynamic ligand exchange for electroreductive Csp3-Csp2 coupling.